Patent GB-388877-A (GB)
Title: Improvements in the manufacture and production of assistants for the textile and allied industries
Filed: 1931-11-28
Abstract: Assistants for the textile and allied industries, of the probable general formula <FORM:0388877/IV/1> where R is an alkyl radicle, R1 is an alkylene radicle, X is an alkyl radicle, which may contain a hydroxyl group, or hydrogen, and Y denotes -- COOZ or -- SO3Z, where Z is hydrogen or an alkali metal, are manufactured by reacting aliphatic aminocarboxylic acids or aliphatic aminosulphonic acids with chlorocarbonic esters of primary or secondary mono- or dihydric open chain aliphatic or cycloaliphatic alcohols (obtainable by acting on the alcohols with phosgene at 0 DEG  C, a small amount of an indifferent solvent, e.g. carbon tetrachloride, being preferably added in the case of solid alcohols), e.g. the chlorocarbonic esters of methyl, ethyl, propyl or butyl alcohols, or glycols such as ethylene, propylene or 1 : 3-butylene glycols, but preferably of alcohols containing more than four carbon atoms, e.g. amyl, n-hexyl, cyclohexyl, decyl, lauryl, octodecyl and oleyl alcohols, octodecandiol and chlorinated alcohols such as dichloroctodecyl alcohol, also alcohols obtainable by catalytic reduction of the acids of montan wax or those resulting from the oxidation of paraffin wax, paraffin oil or like hydrocarbon mixtures, esters of alcohols containing 10 to 20 carbon atoms giving the best results. Mixtures of chlorocarbonic esters from mixtures of different alcohols may also be employed.  As aminocarboxylic or aminosulphonic acids may be employed glycocoll, alanine, sarcosine, aminomethanesulphonic acid, aminoethanesulphonic acid (taurine), N-hydroxyethyltaurine (obtainable by heating hydroxyethylamine and chlorethanesulphonic acid in a closed vessel), aminopropanesulphonic acid, N-methyltaurine, N-butyltaurine (obtainable by heating n-butylamine and chlorethanesulphonic acid in a closed vessel), N-hexyltaurines (obtainable similarly from hexylamine), and the N-hydroxyalkylaminocarboxylic acids obtainable by saponifying the nitriles prepared according to Specification 388,874, e.g. N-2-hydroxyethylaminoacetic acid, N-2-hydroxypropylaminoacetic acid, N-hydroxyethylamino - C - n - propylacetic acid and N-hydroxyethylamino - C - methylethylacetic acid.  The condensation is preferably carried out in the presence of sufficient alkali to neutralize the hydrochloric acid formed, the alkali, e.g. sodium or potassium hydroxides or carbonates or calcium hydroxide, being usually employed as an aqueous solution. The reaction is preferably carried out at 0-80 DEG  C.  Alternatively the chlorocarbonic ester is introduced into an aqueous solution of the alkali metal salts of the amino acids.  The alkali chlorides formed as bye-products may be left in the reaction products without impairing their properties, or may be removed.  The products may be employed in the textile, paper, leather and like industries, e.g. as wetting, dispersing or cleaning agents in washing, fulling, carbonizing, mercerizing, bucking, dyeing and dressing in the softening of artificial silk and the treatment of hides or leather.  They may be employed in acid, neutral or alkaline treatment baths without deposits of difficulty soluble salts even when using water containing lime.  They are particularly useful in the parchmentizing or mercerizing treatment of cotton fabrics or paper with concentrated sulphuric acid for accelerating the wetting of the cellulose.  Those prepared from aminosulphonic acids are particularly valuable as washing and scouring agents, whereas those from amino-carboxylic acids are useful in softening artificial silk. The products are also suitable as dispersing agents for dyestuffs, resins, waxes, paraffin oils or waxes, mineral or vegetable oils or fats and organic solvents.  They may be used alone or with other substances such as soaps, Turkey red oils or dispersive sulphuric esters of other aliphatic compounds or sulphonic acids of high molecular aliphatic or aromatic compounds, or with salts, such as perborates, Glauber's salt or tartaric acid salts or with glue, gum arabic or dextrine, or in conjunction with organic solvents such as cyclohexanol, tetrahydronaphthalene, water-insoluble liquid or solid alcohols, e.g. butanol or benzyl alcohol, or ketones.  In examples: (1) glycocoll is dissolved in caustic soda solution and condensed with a mixture of the chlorocarbonic esters of n-nonyl, n-decyl and n-undecyl alcohols (obtainable by the action of phosgene at 0 DEG  C. on a mixture of the alcohols); the product is suitable as a softening agent for artificial silk or leather; (2) as (1), but using the chlorocarbonic ester of octodecyl alcohol (obtainable by the action of phosgene at 0 DEG  C. on octodecyl alcohol); the product is suitable as a softening agent for artificial silk such as that from viscose or acetyl cellulose; (3) as (1), but using the monochlorocarbonic ester of 1 : 3-butylene glycol (obtainable by the action of phosgene at 0 DEG  C. on the glycol); (4) N-methyl taurine sodium salt is condensed in the presence of caustic soda with the monochlorocarbonic ester of octodecandiol (obtainable by the action of phosgene at 0 DEG  C. on octodecandiol); the product is suitable as washing agent; (5) the sodium salt of N-butylaminoethanesulphonic acid is condensed in the presence of caustic soda with the chlorocarbonic ester of cyclohexanol; the product is suitable as a wetting agent for mercerizing lyes; (6) the sodium salt of hydroxyethylglycocoll is condensed in the presence of caustic soda with the monochlorocarbonic ester of octodecandiol; the product may be used as a softening agent for artificial silk; (7) the sodium salt of N-hydroxylethylaminoethanesulphonic acid is condensed in the presence of caustic soda with the chlorocarbonic ester of octodecyl alcohol; the product is useful as a washing and scouring agent; the chlorocarbonic ester may be replaced by the ester of dichloroctodecyl alcohol (obtainable by chlorinating the chlorocarbonic ester of octodecyl alcohol).ALSO:Compounds of the general formula: <FORM:0388877/III/1> where R is an alkyl radicle, R1 is an alkylene radicle, X is an alkyl radicle, which may contain a hydroxyl group, or hydrogen, and Y denotes -- COOZ or -- SO3Z where Z is hydrogen or an alkali metal, may be used as dispersing agents for dyestuffs, resins, waxes, paraffin oils or waxes, mineral or vegetable oils or fats and organic solvents, or as washing agents, alone or in admixture with other substances such as soaps, Turkey red oils or dispersive sulphuric esters of other aliphatic compounds or sulphonic acids of high molecular aliphatic or aromatic compounds, or with salts such as perborates, Glauber's salts or tartaric acid salts or with glue, gum arabic or dextrine, or in conjunction with organic solvents such as cyclohexanol, tetrahydronaphthalene, water-insoluble liquid or solid alcohols, e.g. butanol or benzyl alcohol, or ketones. Specification 388,874, [Group IV], is referred to.